The best city hikes and walks in Cumberland County
4.8
(89)
1,534
hikers
30
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Urban hiking trails in Cumberland County offer diverse landscapes, from coastal promenades to greenbelt walkways. The region features a mix of waterfront paths, urban parks, and converted rail-trails, providing accessible routes within developed areas. Elevation changes are generally mild, making many trails suitable for various fitness levels. The terrain often includes paved surfaces, crushed stone, and natural paths through urban green spaces.
Best urban hiking trails in Cumberland County
- The most popular urban hiking route is Eastern Promenade Trail,…
Last updated: April 25, 2026
6
hikers
3.72km
00:57
10m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
12.9km
03:17
30m
30m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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3.64km
00:59
60m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
50
hikers
4.64km
01:12
30m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
3.0
(1)
45
hikers
7.59km
01:58
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Other adventures in Cumberland County
Tips from the Community
In the 1800s, cattle once roamed the grassy slopes of Portland’s Eastern Promenade. But as the city grew, so did interest in preserving this scenic area. Historian William Goold and Mayor James P. Baxter played key roles in securing land with views over Casco Bay. By 1905, the Olmsted Brothers were asked to shape the park’s design. Today, the Eastern Prom remains a vital green space.
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This memorial celebrates Portland's founder, George Cleeves, and his partner Richard Tucker, who landed at the historic Portland Waterfront in 1633. From here you get sweeping views out across Casco Bay and the Eastern Promenade. This was the first public monument erected in Portland, two hundred and fifty years after the first colonial landing, in 1883.
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Nestled on the wharf, Scales specializes in classic New England seafood. If you are looking for the finest plates of lobster, octopus, or oysters, this is it! You will need a reservation weeks in advance, which you can find on their website here: https://www.scalesrestaurant.com.
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A place with a nice overlook. Good to have a short stop.
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The Maine Narrow Gauge Railroad Co. & Museum has maintained a narrow gauge railway since 1993, which runs approximately 2.4 km along the coast of the Portland Peninsula and parallel to the Eastern Promenade Trail. The railway tracks date from a time when the Atlantic & St. Lawrence Railroad and later the Grand Trunk Railroad ran from Portland to Montreal. After the East End Rail Bridge was badly damaged by fire in 1984 and was not repaired for economic reasons, the railway line was no longer used. This led to the founding of the non-profit organization with the aim of preserving the railway and making its history unforgettable. https://mainenarrowgauge.org/
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The Eastern Promenade was designed in 1905 by the Olmsted Brothers. The firm is known for designing New York's Central Park and Boston Common. The three-kilometer-long Eastern Promenade Trail runs along the shore of Casco Bay from the northeast of the Portland Peninsula below Munjoy Hill to Portland Harbor. At Tukey's Bridge on Highway 295, there are connections to the Back Cove Trail and the Bayside Trail. The Maine Narrow Gauge Railroad runs special trains along the promenade year-round. https://easternpromenade.org/the-eastern-promenade
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The Atlantic bay off Portland is called 'Casco Bay'. The approximately 520 sq km bay is part of the Gulf of Maine and lies between Cape Elizabeth south of Portland and Cape Small, a peninsula in eastern Maine that extends far into the Atlantic. Six inhabited islands lie in the bay and can be reached by ferry all year round. You can find detailed information about the bay on the website of the 'Friends of Casco Bay - Casco BAYKEEPER'. https://www.cascobay.org/casco-bay/
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We went on a whale watching tour. We spotted a humpback whale mother and calf. Incredibly impressive! Very difficult to photograph. You see the blow briefly, then a back and the whale is gone again. You almost never get to see them jumping out of the water, as you see in photos...
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Frequently Asked Questions
How many urban hiking trails are available in Cumberland County?
You'll find over 30 urban hiking trails in Cumberland County, offering a variety of experiences for all skill levels. Most of these, around 24, are rated as easy, making them accessible for many.
Are there easy urban hikes suitable for beginners or families?
Yes, Cumberland County offers many easy urban hikes perfect for beginners and families. The Eastern Promenade Trail and the Western Promenade Path are both excellent, gentle options within urban settings. For a slightly longer but still easy experience, consider the South Portland Greenbelt Walkway.
Can I bring my dog on urban hiking trails in Cumberland County?
Many urban trails in Cumberland County are dog-friendly, but it's always best to check specific regulations for each trail or park. Generally, dogs are welcome on leash. The Eastern Promenade Trail is a popular choice for dog walkers.
Are there any urban trails with scenic views or interesting landmarks?
Absolutely! Urban trails in Cumberland County often feature beautiful views and landmarks. The Eastern Promenade Trail offers stunning coastal vistas and views of Portland Harbor. The Western Promenade Path provides elevated city views. You can also explore the Portland Head Light at Fort Williams Park, a historic lighthouse, or the tranquil Fore River Sanctuary.
Are there any waterfalls along urban hiking trails in Cumberland County?
While not directly on the urban trails listed, Cumberland County does feature beautiful waterfalls nearby. You can find Jewell Falls and Steep Falls Waterfall within the broader region, offering a natural escape not far from urban areas.
What are some good options for a circular urban hike?
For a pleasant circular urban hike, consider the East End Beach – Eastern Promenade Trail loop from Portland. This route combines scenic coastal paths with the popular Eastern Promenade, offering a varied experience. Another option is the East End Beach – Portland Harbor loop from Portland, which provides a longer circuit around the harbor area.
What do other hikers enjoy most about urban hiking in Cumberland County?
The komoot community highly rates urban hiking in Cumberland County, with an average score of 4.7 stars. Reviewers often praise the accessibility of trails, the beautiful coastal and city views, and the well-maintained paths that make for enjoyable walks. The blend of urban convenience with natural beauty is frequently highlighted.
Are there any less crowded urban trails for a peaceful experience?
While popular trails like the Eastern Promenade can get busy, exploring sections of the South Portland Greenbelt Walkway during off-peak hours or weekdays can offer a more peaceful experience. Additionally, exploring smaller local parks or lesser-known sections of larger trail networks might provide more solitude.
What should I consider bringing for an urban hike in Cumberland County?
For urban hikes in Cumberland County, comfortable walking shoes are essential. Depending on the weather, bring layers of clothing, water, and sun protection. If you plan to explore longer routes like the South Portland Greenbelt Walkway, snacks are also a good idea. Don't forget your camera for the scenic views!
Are there urban trails suitable for winter hiking?
Many urban trails in Cumberland County remain accessible and enjoyable during winter, especially those that are paved or well-maintained. Trails like the Eastern Promenade Trail can offer crisp, scenic walks with unique winter views. Always check local conditions for ice or snow before heading out, and wear appropriate footwear.
Are there any urban trails that are wheelchair accessible?
While specific accessibility details vary, many urban trails in Cumberland County, particularly paved sections of greenways and promenades, are designed to be accessible. The LeTort Spring Run and Nature Trail in Cumberland County, PA, is noted for being handicapped-accessible with a crushed stone path. For trails in the guide, the paved sections of the Eastern Promenade Trail and Western Promenade Path are generally suitable for wheelchairs.
Can I find coffee shops or places to eat near urban trails?
Yes, one of the benefits of urban hiking in Cumberland County is the proximity to amenities. Trails like the Eastern Promenade Trail and Western Promenade Path are often close to vibrant neighborhoods in Portland, where you can easily find coffee shops, cafes, and restaurants to refuel after your walk.
Most popular routes in Cumberland County
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